Basic product and process of making it



Patented Jan. 17, 1933 UNITED STATES PATENT OFFICE ROBERT KNOLL, OF HORNAU IN TAUN'U'S, GERMANY, ASSIGNOR, BY MESNE ASSIGN- MENTS, TO WINTHROP CHEMICAL COMPANY, INC, OF NEW YORK, N. Y., A. CORPORA- TION OF NEW YORK BLASIC PRODUCT AND PROCESS OF MAKING IT No Drawing. Application filed July 30, 1929, Serial No. 382,290, and in Germany August 13, 1928.

The present invention relates to basic products and process of making them, partlcular- 1y to compounds of the following general formula:

wherein R stands for an aliphatic hydrocarbon residue containing at least ten carbon atoms, R stands for O or NH and R stands for an aliphatic residue with a tertiary am no group or for anamino group which contains at least an aliphatic residue with a tertiary nitrogen atom.

These compounds are suitable for therapeutical and technical purposes and are obtained if imino ethers of higher fatty acids or the acids from which these imino ethers are derived, or the esters, chlorides and amides thereof, are condensed with aromatic primary or secondary amines, containing a basic side chain with tertiary nitrogen, for instance with para-,B-diethylamino-ethoxyaniline, or with para-aminobenzoyl-diethylamino ethanol or with methyldiethylaminoethyl-paraphenylene-diamine or with ethyldiethylaminoethyl-para-phenylenediamine. The process may also be carried out by condensing the said acids and acid derivatives with aromatic primary or secondary amines with no basic side chain'and subsequently introducing a basic side chain into the products thus obtained.

The following examples serve to illustrate my invention, but they are not intended to limit it thereto.

(1) 10.4 g. of para-B-diethylaminoethoxyanilene, dissolved in 40 ccm. of dry acetoneand 15 g. of the chloride of oleic acid dissolved in 20 ccm. of acetone are mixed while cooling. After having allowed themixture acetone, melts at 85 C.87 C. By treating it with-an alkali the free base is obtained as a fat-like mass. The aqueous solutions of'the salts, for instance of the benzoate, the lactate or the' salt of the para-phenolsulfon ic'acid,

yield jellies, even when only slightly. concentrated.

The product has the following formula:

ly added thereto. After'eooling the mass is filtered by suction. The resulting hydrochloride which is obtained in the form of colorless laminae, melts at 108 (l-lll"v C. By treating it with an alkali the base is obtained, which recrystallizes from acetone alcohol in the form of felted needles melting at 82 C.

The product has the following formula:

(3) 11.8 g. of the vdiethylaminoethanol ester of para-aminobenzoic acid are dissolved in 20 ccm. of acetone and there are added 13.7 g. of the chloride of palmitic acid in 20 ccm. of acetone. After cooling, the solution is filtered by suction. The hydrochloride of the new compound, when recrystallized from acetone, is'obtaine'd in the form of white laminae melting at 116 C.

The product has the following formula:

-' v -\C zH6 (4) 22.1 g. of asymmetric methyldiethyl' ammoethyl para phenylenediamine dissolved in ccm. of acetic ester and 30 g. of the chloride of oleic acid in 50 com. of acetic ester are mixed. On cooling, the hydrochloride of the new compound crystallizes in the form of colorless laminae.

The product has the following fomnula:

(5) 64.7 g. of asymmetric ethyldiethylaminoethyl-para-phenlyenediamine in 450 ccm. of dry acetone are gradually mixed with 7 5 g. of the chloride of palmitic acid in 250 ccm..

of acetone. After cooling, the hydrochloride of the new compound crystallizes in the form of white druses melting at 81 C.

The product has the following formula:

I claim 1. The process which consists in causing a derivative of a higher fatty acid of the general formula:

wherein R stands for an aliphatic hydrocarbon residue containing at least 10 carbon atoms, R stands for a radical of the group consisting of OH, OCH, OC2H OGH2G Hg, C1, NH and R stands for O or NH, to act upon an aromatic polyamino compound of the following general formula:

wherein R stands for an aliphatic residue with a tertiary amino group or for an amino group which has at least one aliphatic residue containing a tertiary nitrogen.

2. The process whlch consists in causing a chloride of a higher fatty acid of the general formula:

wherein R stands for an aliphatic hydrocarbon residue with at least 10 carbon atoms, to act upon an aromatic polyamino compound of the following general formula:

wherein R stands for an aliphatic residue with a tertiary amino group or for an' amino group which has at least one aliphatic residue containing a tertiary nitrogen.

3. The process which consists in causing a chloride of a higher fatty acid of the gen eral formula:

o RO 01 wherein R stands for an aliphatic hydrocarbon resldue containing at least 10 carbon atoms, to act upon a compound of the general formula:

wherein R stands for hydrogen, an alkyl or an aralkyl and R stands for an aliphatic residue containing a tertiary nitrogen atom.

4. The process which consists in causing a chloride of a higher fatty acid of the general formula:

wherein R stands for an aliphatic hydrocar;

bon residue containing at least 10 carbon.

atoms, to act upon a compound of the formula \C2H4N (C2Ht):

wherein R stands for CH 0r C l-I 5. As new products, the compounds of the following formula:

wherein R stands for an aliphatic hydrocarbon residue containing at least 10 carbon atoms, R stands for O or NH and R stands for an aliphatic residue with a tertiary amino group or for an amino group which contains at least an aliphatic residue with a tertiary nitrogen atom, said products possessing valuable therapeutic and technical properties.

6. As new products, the compounds of the following formula:

wherein R stands for an aliphatic hydrocarbon residue containing at least 10 carbon atoms, R stands for hydrogen or alkyl and R stands for an aliphatic residue with a tertiary nitrogen, said products possessing valuable therapeutical and technical properties. 7. As new products, the compounds of the following formula:

wherein R stands for an aliphatic hydrocarbon residue containing at least 10 carbon atoms, said products possessing valuable therapeutical and technical properties.

following formula:

cal and technical properties.

, I Cfls -sa'id products possessing valuable therapeuti- In testimony whereof, I afiix my s' ature.

ROBERT 

